On Wednesday, we looked at a few random moments in the history of the intersection of Randolph and Dearborn.

We saw a 1909 photo of a midday rush of streetcars and horse-drawn carriages, heard a one-legged booking agent’s 1919 vaudeville memories. I capped that article when the intersection was the hub of the theater district in the 1930s, with the full intention of spending this one going to the ‘50s, going to the ‘70s and then going to bed.

So, well past the midnight hour, let’s see what the intersection with the McDonald’s, Daley Center, Goodman Theatre bar and that angry street preacher with the portable speakers looked like in the early days of Chicago.

1836, Charles C. P. Holden

“It was principally prairie with some timber southerly from Randolph Street, though there were some groups of buildings scattered here and there with small patches of ground inclosed with rail fences,” a man named Charles C. P. Holden told the Chicago Tribune in 1887.

While Randolph Street was the edge of town in 1836, Dearborn was “the lively street,” with the wooden drawbridge built two years prior pulling business to the street.

In 1832, a corner of our little intersection at Randolph and Dearborn sold for $60.

In 1836, the southwest corner sold for $7,800.

In 1839, Mayor William Butler Ogden valued the southwest corner at $350. He said it could fetch as little as $200 in a forced sale, adding “it at least seems questionable” to set the price at a time “when no one has any money to buy property at any price.”

A canal and a bank crisis were to blame.

The Illinois and Michigan Canal was an idea batted around since the fur trapper days of 1673, but had started to become a real plan in the 1820s. Lake Michigan wasn’t connected to the Mississippi in any way, so traders had to get out of the lake and walk their cargo to the nearest waterway that would get them to the Mississippi.

But a canal connecting the two, say one running from Chicago to the Illinois River at LaSalle 96 miles away, why that would be great.

Especially for people who owned land in Chicago.

The town that had been 12 houses in 1830 became a boom town, with speculators coming in from across the nation to snatch up cheap land and sell it for a fortune. One lot on Water Street by Wells sold for $66 in October 1833 and $800 a month later.

When the speculative spirit flagged, auctioneers were there to whip the crowd back into a frenzy with tales of fortunes made and easy money in Chicago real estate.

“Where bodies of men, actuated by a common motive, assemble together for a common object, zeal is apt to run to enthusiasm when the common passion is artfully inflamed by a skillful orator, enthusiasm becomes fanaticism, and fanaticism, madness,” one account of the time wrote.

Work started on the canal in 1836, the $7,800 year for our little corner.

Then, crash. The Crisis of 1839 (not to be confused with the Panic of 1837, proving you shouldn’t be a banker in the 1830s) hit the State Bank of Illinois, which was already reeling from canal debt and other big infrastructure projects.

In today’s money, the value of our corner at Dearborn and Randolph went from $1,441 to $170,253 to $4,502 in seven years.

A rerouting of the cable cars in 1888 turned Dearborn into one of the legs of a pre-Loop loop, raising the street “from a place of obscurity to one of the most prominent office streets of Chicago in 1889,” Hoyt and Millis wrote.

Randolph and Dearborn was one of the pre-Loop’s corners.

1950, Jack Lait and Lee Mortimer

“Cocktail lounges with hookers; horse rooms; lawyers’ offices,” is how a book called “Chicago: Confidential!” described the Dearborn Street of the post-WWII year.

It sets Randolph Street in a bit more color, calling it “Theatrical, Tin Pan Alley, politico-legal center. Hookers on the street and B Girls in the ‘Theatre Bars.’”

“Chicago: Confidential!” is a 1950 guide to the sinny side of Chicago, complete with appendix at the end listing how much your seduction, fornication, statutory rape, abortion or bigamy will net you under Illinois sex laws of the time.

In a chapter called “Wolf-Bait,” describing the various lovelies who might necessitate a 1950 creepo to consult that appendix, it talks of the glory days of Chicago’s vaudeville life as a far distant memory.

“We don’t want to make you cry, little girl,” the book continues. “But if you want to sell glamor or talent and don’t want to sell it in a burlesque way, keep heading all the way West or all the way East.”

B Girls, by the by, were low-level seductresses paid by bars to flirt with men to get them to buy more drinks. Lee Mortimer and Jack Lait, the authors of the “Confidential!” series of sex and sin across the nation put B Girls in their personal hierarchy of tail below the “26 girls” who work craps tables but above an “out-and-out whore with no shame and no strings.”

Mortimer looked more the type for sleaze and sin. Flash suit with perfectly coiffed light hair, Mortimer looks stylish and angry in his most famous photo — the one at the courthouse after Frank Sinatra decked him.

As anti-communist as he was pro-sleaze, Mortimer had been attacking Sinatra in his column as a tool of both the Mafia and the Reds, using information personally sent to him by Hoover’s right hand Clyde Tolson. At a night club in West Hollywood in 1947, Mortimer whispered “dago” to Sinatra as the two passed each other and the singer decked the columnist. Sinatra later paid Mortimer $9,000 to settle out of court.

And speaking of people Sinatra threatened to slug…

1971, Mike Royko

More trustworthy but no less depressing than “Chicago: Confidential!” is Mike Royko’s 1971 masterwork “Boss: Richard J. Daley of Chicago,” a no-holds-barred biography of Chicago’s first Mayor Daley.

Daley started the Civic Center project at our corner in the early 1960s. It would buy up and demolish an entire city block of restaurants, bars, stores and other businesses — including Henrici’s, then Chicago’s oldest restaurant — to put up a towering glass-and-steel skyscraper on the southwest corner of the intersection where the cable cars once looped, vaudevillians once loitered and prices went from $60 to $7,800, then crashed again.

“He put it all there, the Civic Center, the plaza, the Picasso. And the judges and county officials who work in the Civic Center, he put most of them there, too,” Royko wrote in “Boss.”

Yes, the corner we’ve tracked from real estate land grabs to vaudeville haven to smut and sin now houses the Daley Center. Blues Brothers chase scene. Christkindlmarket. The big, famous Picasso sculpture.

In a column after the 1967 unveiling of the Picasso, Royko let loose on the now-famous sculpture. He gave it the worst criticism he could muster, that it fit.

“… it has a long stupid face and looks like some giant insect that is about to eat a smaller, weaker insect. It has eyes that are pitiless, cold, mean.

“But why not? Everybody said it had the spirit of Chicago. And from thousands of miles away, accidentally or on purpose, Picasso captured it.”